Hydrochloric Acid → HCID 22344578, compound

HRID 2299786Notes

Reaction equation

HRID 2299786 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](/[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)\[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[CH2:18][C:19]1[CH:38]=[CH:37][C:22]([O:23][CH2:24][C:25]2[N:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:28][C:29]=2[CH3:30])=[CH:21][CH:20]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH3:30][C:29]1[O:28][C:27]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:26][C:25]=1[CH2:24][O:23][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:3]/[N:4]=[C:5](/[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)\[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:38][CH:37]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 15169611HCID 15169611, compound

Product 1

HCID 22344578HCID 22344578, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Sodium hydride (60% in oil, 153 mg) was added to a solution of ethyl Z-2-hydroxyimino-2-(3-pyridyl)acetate (619 mg) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.00 g) in N,N-dimethylformamide (10 ml) at room temperature under nitrogen atmosphere and stirred for 3 hours. 1N hydrochloric acid (7 ml) was added, an aqueous saturated solution of sodium bicarbonate was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl Z-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-(3-pyridyl)acetate (1.12 g, yield 74%) as a pale-yellow oil from an ethyl acetate-hexane (1:1, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8d81b9f6e9a459a9b3c466841166a85
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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